Abstract
The kinetics of oxidation of glycine by N-bromophthalimide (NBP) were studied in the presence of an anionic surfactant, sodium dodecyl sulfate, in acidic medium at 308 K. The rate of reaction was found to have first-order dependence on [NBP] and fractional-order dependence on [glycine] and [H+]. The addition of reduced product of the oxidant had no significant effect on the rate of reaction. Increasing [Hg(OAc)2] and [Br−] increased the rate of reaction, whereas a change in ionic strength (μ) of the medium had no effect on oxidation velocity. The rate of reaction decreased with a decrease in dielectric constant of the medium. HCN was identified as the main oxidation product of the reactions. The various activation parameters have been computed. A suitable mechanism consistent with the experimental findings has been proposed. The index of cooperativity and the micelle binding constant have been calculated.
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Abbreviations
- CMC:
-
critical micelle concentration
- NBP:
-
N-bromophthalimide
- NBS:
-
N-bromosuccinimide
- NBSA:
-
N-bromosaccharin
- SDS:
-
sodium dodecyl sulfate
References
Chiarini, M., G. Cerichelli, H.J. Foroudian, N.D. Gillitt, S.F. Yunes, and C.A. Bunton, Oxidation of Thioanisole by Peroxomolybdate in Assemblies of Cetyl Pyridinium Chloride and Methyltri-N-octylammonium Chloride, Langmuir 20:5201 (2004).
Chiarini, M., and C.A. Bunton, Peroxomolybdate Mediated Oxidation of Thioanisole in Cationic and Anionic Microemulsions. Direct and Indirect Oxygen Transfer, Colloid Surf. A 245:177 (2004).
Chiarini, M., N.D. Gillitt, and C.A. Bunton, The Oxidation of Thioanisole by Peroxomolybdate in Micelles of Cetyl Pyridinium Chloride, Langmuir 18(10):3836 (2002).
Chiarini, M., and C.A. Bunton, Oxidation of Thioanisole by Peroxomolybdate in Alcohol-Modified Micelles of Cetyl Pyridinium Chloride, Langmuir 18:8806 (2002).
Makote, R.D., and C. Chatterjee, Kinetics and Mechanism of Oxidation of Ascorbic Acid by Cobalt (III) Complexes in Micellar Medium, Ind. J. Chem. 37A:21 (1998).
Panigrahi, G.P., and S.K. Mishra, Micellar Effect in the Oxidation of Malic Acid by Chromic Acid, Ind. J. Chem. 32A:956 (1993).
Hussain, M., and F. Ahmad, Effect of Micelles on Kinetics and Mechanism of the Oxidation of Serine by Acid Permanganate, Int. J. Chem. Kinet. 22:321 (1990).
Nagar, V., S.K. Solanki, and V.R. Shastry, Kinetic Studies in the Mechanism of Micellar Catalysed Oxidation of Monoamino-monocarboxylic Acids by Chloramine-T in Acidic Medium, J. Ind. Chem. Soc. 67:956 (1990).
Sanchez, F., M.L. Moya, A. Rodriguez, R. Jimenez, C. Gomez-Herrera, C. Yanes, and P. Lopez-Cornejo, Micellar, Microemulsion and Salt Kinetic Effect upon the Reaction Fe(CN)2 (bpy)2+S2O 2−8 , Langmuir 13:3084 (1997).
Khan, Z., S.I. Ali, Md. Z.A. Rafiquee, and Kabir-ud-Din, Influence of Cationic and Anionic Micelles on the Reactions of Ninhydrin with Different Amino Acids. A Kinetic Study, Ind. J. Chem. 36A:579 (1997).
Panigrahi, G.P., and R. Swain, Kinetics and Mechanism of Oxidation of Hydroxylaminehydrochloride by Vanadium(V) in the Presence of Sodium Lauryl Sulphate, Int. J. Chem. 40A:1191 (2001).
Panda, J., and G.P. Panigrahi, Kinetic Investigation of the Oxidation of Sulphanilic Acid by Peroxomonophosphoric Acid in Anionic Surfactant Sodium Lauryl Sulphate, Ind. J. Chem. 42A(7):1636 (2003).
Kabir-ud-Din, U. Salma, and Z. Khan, Effect of CTAB Micelle on the l-Isoleucine-Ninhydrin Reaction, J. Surf. Sci. Technol. 36:101 (2003).
Kabir-ud-Din, J.K. Salem, and S. Kumar, Micellar and Salt Effects on the Ruhemann's Purple Formation Between l-Lysine and Ninhydrin, Ind. J. Chem. 39A:1019 (2000).
Kabir-ud-Din, A.M.A. Morshed, and Z. Khan, Micellar Effects on the Oxidation of d-Glucose by Chromic Acid in Perchloric Acidic Medium, J. Carbohydr. Chem. 22:843 (2003).
Bhagwat V.W., M. Pipada, S.B. Jonalagadda, and B. Pare, Kinetics and Mechanism of C16TAB Catalysed Oxidation of Methylene Violet by Chloramine-T in Acidic Medium, Ind. J. Chem. 42A:1644 (2003).
Gemeay, A.H., I.A. Mansour, R.G. El-Sharkawy, and A.B. Zaki, Catalytic Effect of Supported Metal Ion Complexes on the Induced Oxidative Degradation of Pyrocatechol Violet by Hydrogen Peroxide, J. Colloid Interface Sci. 263:228 (2003).
Wang, P.J., W.T. Lee, W.H. Hwu, C. Young, K.T. Yau and Y.Z. Shen, The Controversy Regarding Diagnostic Criteria for Early Myoclonic Encephalopathy. Brain Dev. 20:530 (1998).
Jabbar, S.F.A., and V.S. Rao, Kinetics of Oxidative Deamination of Aliphatic Amines by N-Bromophthalimide in Aqueous Acetic Acid Medium, Ind. J. Chem. 33A:69 (1994).
Anjum, A., and P. Srinivas, Kinetics and Mechanistic Aspects of Oxidation of Acetophenones by N-Bromophthalimide in Presence of Mercuric Acetate, Asian J. Chem. 17:553 (2005).
Khan, S., S.K. Nigam, H.P. Dwivedi, and P.K. Singh, Oxidative Degradation of Methyl Ethyl Ketone by N-Chlorosaccharin, Asian. J. Chem. 16:751 (2004).
Thiagarajan, V., and S. Ramakrishnan, Oxidation of α-Hydroxyacids by N-Bromophthalimide-Dependence of Mechanism on pH of the Medium, Ind. J. Chem. 37B:443 (1998).
Ramachandrappa, R., Puttaswamy, S.M. Mayanna, and N.M.M. Gowda, Kinetics and Mechanism of Oxidation of Aspirin by Bromamine-T, N-Bromosuccinimide and N-Bromophthalimide, Int. J. Chem. Kinet. 30(6):407 (1998).
Kumar, K.G., and P. Indrasenan, Titrimetric Determination of para-Amino Benzoic Acid Using N-Bromophthalimide and N-Bromosaccharin, J. Pharm. Biomed. Anal. (UK) 7:627 (1989).
Kumar, K.G., and P. Indrasenan, Titrimetric Methods for the Determination of Some Sulpha Drugs Using N-Bromophthalimide and N-Bromosaccharin, Analyst (London) 113:1369 (1988).
Kumar, K.G., C.M. Das, and P. Indrasenan, Determination of Some Carbohydrates with N-Bromophthalimide and N-Bromosaccharin, Talanta (UK) 35:651 (1988).
Singh, A.K., V. Singh A.K. Singh, N. Gupta, and B. Singh, Kinetics and Mechanism of Ru(III) and Hg(II) Co-catalyzed Oxidation of d-Galactose and d-Ribose by N-Bromoacetamide in Perchloric Acid, Carbohydr. Res. 337:345 (2002).
Gowda, B.T., and P. Ramachandra, Kinetics and Mechanism of Ru(III)-Catalysed Oxidation of Amino Acids by N-Chlorosodio-toluence-p-sulphonamide in Acid Media, Proc. Ind. Acad. Sci. (Chem. Sci.) 102(1):7 (1990).
Farook, N.A.M., R. Prabaharan, and R. Senthil, Kinetics of Oxidation of Some Amino Acids by N-Halo Compounds in Aqueous Acetic Acid Medium, Ej. Chem. 1(2):127 (2004).
Farook, N.A.M., G.A. Seyed Dameem, Kangaraj and Murugesan, Kinetics of Oxidation of Some Essential Amino Acids by N-Chlorosaccharin in Aqueous Acetic Acid Medium, E-J. Chem. 1(2):132 (2004).
Pink, J.M., and R. Stewart, Oxidation of Mandelic Acid by Bromine, Canad. J. Chem., 49(4):650 (1971).
Abou, O., M.I. Walash, M. El-Kerdawy, and El-Ashry, Evaluation of Certain Pharmaceuticals with N-Bromophthalimide. Part I. The Determination of Sulphonamides, J. Drug Res. 12:77 (1980).
Barkat, M.Z., and M.F.A. El-Wahab, Microdetermination of Bromine or Chlorine in N-Halogenated Imides, Anal. Chem. 26:1973 (1954).
Soloway, S., and A. Lipschietz, Colorimetric Test for Amides and Nitriles, Anal. Chem. 24:898 (1952).
Mahadevappa, D.S., S. Ananda, M.B. Madegowda, and K.S. Rangappa, Oxidation of α-Amino Acids with Sodium N-Bromo-p-Toluene Sulphonamide: A Kinetic Study, J. Ind. Chem. Soc. 61(4):323 (1984).
Vijaya, M.K., P.R. Rao, and E.V. Sundaram, N-Bromosaccharin as an Oxidising Agent: A Kinetic Study Using Aliphatic and Cyclic Ketones in Aqueous Acetic Acid, J. Ind. Chem. Soc. 61:225 (1984).
Menger, F.M., and C.E. Portnoy, On the Chemistry of Reactions Proceeding Inside Molecular Aggregates, J. Am. Chem. Soc. 89:4698 (1967).
Bruice, T.C., J. Katzhendler, and L.R. Fedor, Nucleophilic Micelles. II. The Effect on the Rate of Solvolysis of Neutral, Positively and Negatively Charged Esters of Varied Chain Length when Incorporated into Nonfunctional and Functional Micelles of Neutral, Positive and Negative Charge, J. Am. Chem. Soc. 90:1333 (1968).
Piszkiewirz, D., Positive Cooperativity in Micelle Catalyzed Reactions, J. Am. Chem. Soc. 99:1550 (1977).
Hill, A.V., The Possible Effects of the Aggregation of the Molecules of Haemoglobin on Its Dissociation Curve, J. Physiol. 40:4–6 (1910).
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Joshi, G.K., Katre, Y.R. & Singh, A.K. Kinetics of glycine oxidation by N-bromophthalimide in the presence of sodium dodecyl sulfate. J Surfact Deterg 9, 231–235 (2006). https://doi.org/10.1007/s11743-006-5002-3
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DOI: https://doi.org/10.1007/s11743-006-5002-3